Skills

Communication Leadership HubSpot Sales Prospecting CRM Research Organization

Job Specifications

About Company

Join ExpensePoint at an inflection point! Fresh off new investment with ex-Google and Microsoft leadership, we're a nimble Canadian fintech taking on Fortune 500 clients and major banks. We're seeking a driven Account Executive to capitalize on our momentum - combining inbound lead conversion with aggressive outbound prospecting to fuel our explosive growth.

Role Overview

Individual contributor role focused on outbound prospecting and early-stage engagement with potential customers.
Support global sales efforts by identifying target companies, engaging the right buyers, and setting high quality meetings for Account Executives.
Ideal candidate enjoys outbound activity, curious about complex, structured buying organizations and thrives in a high growth remote-first company.

Role Objectives

Generate qualified outbound meetings with mid-market and enterprise prospects
Support consistent pipeline of prospect for the Account Executives
Engage target companies with relevant, personalize outreach
Develop a strong understanding of the company ICP, buyers and value propositions
Execute outbound activities with consistency and discipline

Core Responsibilities

Outbound Prospecting and Lead Generation

Research and identify target companies and buyers in our ICPs
Execute outbound outreach via email, phone, LinkedIn and other channels
Personalize messaging based on company research and prospect context
Book qualified meetings aligned to agreed qualification criteria

Collaborate with Account Executives

Work closely with Account Executives on ICP targeting and outreach strategies
Support account based prospecting into mid-market and enterprise organizations
Share prospect feedback, objections and insights
Ensure clean handoffs and well-prepared meetings

Qualification and Discovery Support

Conduct initial qualification conversations
Identify prospect pain points, priorities and buying signals
Confirm ideal fit before passing opportunities to Account Executives

Process and Tool Discipline

Maintain accurate activity, lead, and account data in the HubSpot CRM
Follow outbound sequences and continuously improve messaging
Track outreach performance and contribute ideas for improvement

Required Experience & Profile

Experience

1- 3+ years of experience in BDR, SDR or outbound sales role
Experience working in a small or growth stage software company
Exposure to mid-market and enterprise selling is a plus
Comfortable supporting global outbound efforts across time zones

Skills and Attributes

Strong written and verbal communication skills
Curious, coachable and motivated to learn
Organized and consistent with outbound execution
Resilient and comfortable with rejection
Able to work independently in a remote-first environment

Preferred Experience (Nice to Have)

Bilingual (English/French) verbal and written
Experience with CRM and sales engagement tools
Familiarity with account based prospecting
HubSpot fluency

What Success looks like in the first 6 months

Consistent delivery of qualified meetings
Strong working relationships with Account Executive
Improving outreach to meeting conversion rates
Solid understanding of ICP, buyers and use cases
Reliable execution and HubSpot CRM hygiene

Tools and Working Environment

HubSpot CRM and sales engagement tools (Lemlist, Apollo)
Access to AI business accounts (ChatGPT, Claude, Gemini)
Remote-first, distributed team environment headquartered in Winnipeg in a modern, fun space
Lean, collaborative sales organization with direct access to decision-makers

Compensation and Benefits

Competitive base salary plus variable compensation
Clear performance targets tied to meetings and pipeline
Benefits and flexibility aligned with a Canadian-based, remote workforce

Why Join?

Exceptional leadership team - founders and senior team from Google, Microsoft, and other top-tier companies
Backed by reputable private equity with recent investment fueling rapid growth
Product transformation - exciting time to join as we revamp our platform with cutting-edge technology
Punch above our weight - small Canadian team selling to Fortune 500 companies and major financial institutions
Career growth opportunity - break into the exciting world of software sales with mentorship from industry veterans
Competitive compensation with opportunities for career progression

About the Company

Trusted by over 70,000 users across 106 countries, ExpensePoint delivers comprehensive expense management for midsize to enterprise organizations. Our intuitive application eliminates reporting frustrations through powerful automation features: advanced mobile receipt capture, GPS mileage tracking, exceptional receipt-to-data conversion and customizable approval workflows. Supporting 14 languages with robust currency and tax management capabilities, ExpensePoint seamlessly connects with all major accounting systems through f... Know more